Sodium Hydroxide → HCID 68868812, compound

HRID 1985169Notes

Reaction equation

HRID 1985169 reaction equation
C([O:3][C:4](=[O:43])[C:5]([CH3:42])([O:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH:16]2[CH2:20][N:19]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=3)[C:18](=[O:32])[N:17]2[CH2:33][CH3:34])=[CH:9][CH:8]=1)C.[OH-].[Na+]>C(O)C>[CH2:33]([N:17]1[CH:16]([CH2:15][CH2:14][O:13][C:10]2[CH:11]=[CH:12][C:7]([CH2:6][C:5]([CH3:42])([O:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:4]([OH:43])=[O:3])=[CH:8][CH:9]=2)[CH2:20][N:19]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:29])([F:31])[F:30])=[CH:24][CH:23]=2)[C:18]1=[O:32])[CH3:34]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10289984HCID 10289984, compound

Product 1

HCID 68868812HCID 68868812, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-(4-{2-[3-Ethyl-2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethoxy}-phenyl)-2-methyl-2-phenoxy-propionic acid ethyl ester (0.31 g, 0.518 mmol) and 5N NaOH (1 mL) in ethanol (9 mL) is refluxed for 1 hour, cooled to ambient temperature, and concentrated. The residue is diluted with CH2Cl2, washed, dried, and concentrated in vacuo to provide the title compound (0.256 g, 87%). 1H NMR (400 MHz, CDCl3): δ 7.54 (d, 2H, J=7.6 Hz), 7.35 (d, 2H, J=8.4 Hz), 7.21-7.17 (m, 4H), 6.97 (t, 1H, J=7.6 Hz), 6.88 (d, 2H, J=7.6 Hz), 6.72 (d, 2H, J=8.4 Hz), 4.42, 4.38 (ABq, 2H, J=15.1 Hz), 3.94 (t, 2H, J=5.9 Hz), 3.87-3.81 (m, 1H), 3.62-3.53 (m, 1H), 3.36 (t, 1H, J=8.4 Hz), 3.31, 3.08 (ABq, 2H, J=8.4 Hz), 3.15-3.08 (m, 1H), 3.00 (t, 1H, J=8.4 Hz), 2.23-2.19 (m, 1H), 1.89-1.82 (m, 1H), 1.37 (s, 3H), 1.13 (t, 3H, J=6.7 Hz). MS [EI+] 571 (M+H)+, [EI−] 569 (M−H)+.

Workup

  1. concentrationconcentrated
  2. additionThe residue is diluted with CH2Cl2
  3. washwashed
  4. customdried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d326b2e92eca407198e0ba39b608fc25
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

Loading…